Halogenized carboxylic acid of the phenylaminoanthraquinone series.



sA'rs FRITZ ULLMAINN, OF CHARLOTTENBURG, GERMANY, ASSIGNOR TO ACTIENGESELL- SCI-IAF'I FUR ANILIN FABRIKATION, F BERLIN, GERMANY.

HALOGENIZED CARBOXYLIO ACID OF THE PHENYLAMINOANTHRAQIIINONE SERIES.

No Drawing.

To all whom it may concern:

Be it known that I, FRITZ ULLMANN, a subject of the King of Bavaria,residing at Charlottenburg, near Berlin, Germany, my post-ofiice addressbeing 15/16 Schillerstrasse, Charlottenburg, near Berlin, Germany, haveinvented certain new and useful Improvements in New HalogenizedCarboxylic Acids of the Phenylaminoanthraquinone Series, of which thefollowing is a specification.

According to my present invention new halogenized carboxylic acids ofthe phenylaminoanthraquinone series are obtained, which contain ahalogen-atom and which are very valuable parent materials for themanufacture of vat dyes as well as of intermediate products for suchdyes.

My invention is based on the observation that alpha-chloroanthraquinonereacts with a halogenized anthranilic acid forming thus a halogenizedalpha-anilidoanthraquinone carboxylic acid; the reaction may berepresented, for instance, by the following equation using abromoanthranilic acid:

COOH

COOH

Ill;

In performing the reaction a substance capable of absorbing thehydrochloric acid formed during the reaction and a body possessing a.so-called catalytic function are added.

The following example illustrates my in vention, the parts being byweight: 24.2 parts of alpha-chloroanthraquinone and 22 parts ofbromoanthranilic acid (NH :COOH:Br:1 12:4)

are dissolved in 462 parts of amyl alcohol; 20 parts of potassiumacetate, 1 part of cop- Specification of Letters Patent.

Application filed March 13, 1911. Serial No. 614,209.

Patented May 30, 1911.

per acetate and 1 part of copper are added and the mixture is heated inthe oil bath at 160 C. while stirring, whereby the mass soon becomesviolet. \Vhen the change is complete, the mass is distilled in steam andthe residue is extracted first with dilute hydrochloric acid and thenwith toluene.

The new alpha-bron1oanilido-anthraquinone carboxylic acid remainsundissolved and is then obtained as a violet powder, melting above 300(1., which dissolves in pyridin to a violet solution and which is insoluble in alcohol and benzene.

My present invention is not limited to the foregoing example or to thedetails given therein. Thus, for instance, instead of'thepara-bromoanthranilic acid used in the above example anotherbromoanthranilic acid or a chloroanthranilic acid may be used. For thecopper or the copper acetate another suitable agent of a so-calledcatalytic function may be substituted. Furthermore I can make use of anyother substance of a kind adapted to absorb the hydrochloric acid formedduring the reaction, and of any suitable solvent.

Having now described my invention and in what manner it may be performedwhat I claim is,-

1. As new articles of manufacture the new halogenized alpha anilidoanthraquinone carboxylic acids possessing the general formula:

in which formula X signifies a halogen, which new bodies can be obtainedby the action of alpha-chloro-anthraquinone upon a halogenizedanthranilic acid in the presence of a substance capable of absorbing thehydrochloric acid formed and of a body of a so-called catalyticfunction. and which new halogenized carboxylic acids by the action of adehydrating agent are converted into a halogenized anthraquinoneacridon, these new bodies being violet powders, insoluble in alcohol andbenzene but soluble in pyridin and possessing a high melting point.

2. As a new article of manufacture the newbromo-alpha-anilido-anthraquinone carboxyl'ic acid possessing thefollowing forilr which can be obtained by acting withalphachl'oroanthraquinone upon broIno-anthranilic acid (NH COOH': Br l2: et) and which new body forms a violet powder V in " melting above 300C. and insoluble in alcohol'and benzenebut soluble in pyridin to aviolet solution,andwhich new brominated ca-rboxylic acid by the actionof a dehydrating agent is converted into the correspond- FRITZ ULLMANN.

Witnesses HENRY HASPER, WOLDEMAR HAUPT.

